TW401396B - Ester compound and pesticide containing thereof - Google Patents

Abstract

The present invention provides 2, 3, 5, 6-tetrafluoro-4-methylbenzyl (1R)-trans-3-(2-methyl-1-propenyl)-2, 2-dimethylcyclopropanecarboxylate and pesticide containing it as an active ingredient. The present pesticide has an excellent pesticidal activity and it is especially suitable for household use.

Description

V. Description of the invention (1) [Field of invention] ff 89 · 3. 06: Amendment The present invention relates to a pyrethroid compound and an insecticide containing the compound. [Background technology] So far it is known that the alcohol component in [3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid] ester is 4-allyl-2 , 3, 5, 6-tetrafluorobenzyl alcohol and 2, 3, 5, 6-tetrafluoro-4-methoxy T-yl alcohol have insecticidal activity (EP-31199-A). However, the insecticidally active ingredients of these ester compounds have not been satisfactory. It is also known that (1R) -cis- 3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid 2, 3, 5, 6 -tetrafluoro-4- Methyl T esters have insecticidal activity against insects in the soil (J. Agric. Food. Chem. (1992), 40 (8), 1432). However, this compound is highly toxic to mammals. Therefore, there is a safety problem when used as an insecticide, especially in a limited living space at home. [Outline of the Invention] The present invention provides (1R) -trans- (3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid 2, 3) represented by the following formula (I): , 5, 6-tetrafluoro-4-methylbenzyl ester (hereinafter referred to as "the present compound"),

And an insecticide containing the compound as an active ingredient.

A: \ 310179.ptc Page 4 2000.03.02.004 V. Description of the invention (1) [Field of invention] ff 89 · 3. 06: The invention relates to a pyrethroid compound and an insecticide containing the compound . [Background technology] So far it is known that the alcohol component in [3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid] ester is 4-allyl-2 , 3, 5, 6-tetrafluorobenzyl alcohol and 2, 3, 5, 6-tetrafluoro-4-methoxy T-yl alcohol have insecticidal activity (EP-31199-A). However, the insecticidally active ingredients of these ester compounds have not been satisfactory. It is also known that (1R) -cis- 3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid 2, 3, 5, 6 -tetrafluoro-4- Methyl T esters have insecticidal activity against insects in the soil (J. Agric. Food. Chem. (1992), 40 (8), 1432). However, this compound is highly toxic to mammals. Therefore, there is a safety problem when used as an insecticide, especially in a limited living space at home. [Outline of the Invention] The present invention provides (1R) -trans- (3- (2-methyl-1-propenyl) -2,2-dimethylcyclopropanecarboxylic acid 2, 3) represented by the following formula (I): , 5, 6-tetrafluoro-4-methylbenzyl ester (hereinafter referred to as "the present compound"),

And an insecticide containing the compound as an active ingredient.

A: \ 310179.ptc Page 4 2000.03.02.004 Public Left SS87118115

Amendment V. Explanation of the invention (12) Compounds, for example, etfenenx [2- (4-ethoxyphenyl) -2-methylpropyl-3-phenylhydrobenzyl mystery], Fenber Fenvaierate [(RS) -a-fluoro-3-phenoxybenzyl (rs) -2- (4-phenyl) -3-fluorenylbutyrate], Yifenbury (63 { 61 ^ & 16 ^ 士 6) [(3)-«-| 1yl-3-phenoxybenzyl (5) -2- (4-aminobenzyl) -3-methylbutyric acid vinegar], fen Fenpr〇pathrin URS)-~ cyano-3-phenoxybenzyl 2, 2, 3, 3-tetramethylcyclopropanecarboxylate], cypermethrin [(RS) _a_ 氱_3_phenoxyfluorenyl (1RS) -cis, trans-3_ (2,2-digasvinyl) -2,2-dimethylcyclopropane sulfonate], permethrin ) [(lRS) -cis, trans-3- (2,2-difluorovinyl) -2,2-dimethylcyclopropanecarboxylic acid 3-phenoxy vinegar], cyhalothrin [(RS) -a-fluoro-3-phenoxy T-group (Z)-(IRS) -cis-3- (2-amino-3, 3, 3 -trifluoroprop-butenyl)- 2, 2-Amidinocyclopropane acetic acid vinegar], deltamethrin [(S) -a ~ fluoro-3 -phenoxy (ir) -cis- 3- (2, 2- Dibromovinyl) -2,2-dimethylcyclopropane vinegar], Cycloprine (CyCl〇pr〇thrin) [(RS) -a ~ Gasoyl-3 -phenoxyTyl (RS) -2, 2-dioxo-1- (4-ethoxyphenyl) cyclopropanecarboxylate ], Fluvalinate (a-fluoro-3-phenoxyT-group N- (2-amino-α, α, trifluoro-p-tolyl) -D-valinate), bifennine (1 ^ [6111 ^ 1 ^ 1〇 [2-methylbiphenyl-3-ylmethyl) (2)-(11 ^) _ cis-3- (2-amino-3, 3, 3-trifluoro Allyl-1-enyl) -2,2-dimethylcyclopropanecarboxylate, 2-methyl-2- (4-bromodifluoromethoxyphenyl) propyl (3-phenoxybenzyl) Mystery, tralomethrin [(S) -α-cyano-3-phenoxybenzyl (1R-cis) 3 {(1RS) (1,2,2,2-tetrabromoethyl)} -2,2-dimethylcyclopropanecarboxylate], silafluofen [(4-ethoxyphenyl) {3- (4-

C: \ Program Files ^) atent \ 310179.ptc Page 15 2000. 03.02.015 V. Description of the invention (2) [Detailed description of the invention] The compound can be an alcohol compound represented by the following formula (H):

(1R) -trans_3- (2_fluorenyl-1-propenyl) -2,2-difluorenylcyclopropanecarboxylic acid with the following formula (Π): 〇

Or its reactive derivative (for example, fluorenyl halide, acid anhydride). The reaction is usually carried out in an inert solvent in the presence of a condensing agent or a base. Examples of the condensing agent include dicyclohexylcarbodiimide (DCC), 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (WSC), and the like. Examples of tests include organic tests / e.g. Triethylamine, hydrazine, NIN-diethylaniline, 4-dimethylaminopyridine, diisopropylethylamine and the like. Examples of solvents used include hydrocarbons such as benzene, toluene, hexane, etc .; ethers such as diethyl ether, tetrahydrofuran, etc .; and halogenated hydrocarbons such as digas methane, 1,2-di

Amendment 401396 LUtf V. Description of the invention (13) Monofluoro-3 -phenoxyphenyl) propyl} Toshinobentane], d-phenothrin [3-phenoxybenzyl (1R ) -Cis, trans) -chrysanthemic acid] fenfenine (〇7 卩 1 ^ 11〇1: 111'111) [(1 ^)-〇: -cyano-3-phenoxybenzyl (11 ? -Cis, trans) -permethrin], d-resmethrin [5-fluorenyl-3 -pyridine methyl (1R-cis, trans) _chrysanthemic acid], g Acrinethrin [(S) -α-fluorenyl-3-phenoxybenzyl (1R-cis (z))-(2, 2-diamidino-3- {3-oxo-3- (1,1,1,3,3,3-hexafluoropropoxy) propenyl} cyclopropanecarboxylate], cyfluthrin [(RS) -a-fluorenyl-4-fluoro- 3-phenoxybenzyl 3- (2, 2-difluorovinyl) -2,2-dimethylcyclopropane carboxylate], deflunine (Shi 60101: 111: 111) [2,3 , 5,6-tetrafluoro-4-methylbenzyl (11 ^ -cis (Z))-3- (2-amino-3, 3,3-trifluoroprop-butenyl) -2 , 2-dimethylcyclopropane carboxylic acid], transfluthrin [2,3,5,6-tetrafluoro (1R-trans) -3- (2, 2 -digas vinyl) ) -2,2-Dimethylcyclopropanecarboxylic acid vinegar], tetramethine rin) [3,4,5,6-Tetraarginophthalimideiminofluorenyl (1RS) -cis, trans-chrysanthemate], al lethrin [(RS) -3-allyl 2-methyl-4-oxocyclopent-2-enyl (1RS) -cis, trans-chrysanthrin], pallethrin (; (s) _2-methyl_4 _Oxo_3_ (2-propanyl) cyclopent-2-enyl (1R) _cis, trans-chrysanthemate], empenthrin [(RS) -buethynyl-2 -Methyl-2-pentenyl (1R) -cis'trans-chrysanthemate], imiprothrin [2,5-dioxo-3- (prop-2-ynyl) Imidazolidinylmethyl (1R) _cis, trans_2, 2_dimethyl-3- (2-fluorenylprop-1-enyl) cyclopropanecarboxylate], fenminin (d_fUramethrin) [5- (2-propynyl) furyl (1R) _cis, trans-chrysanthemic acid], and 5- (2-propynyl) furanmethyl 2, 2, 3, 3 tetramethyl Cyclopropane

C: \ Program Files \ patent \ 310179.ptc Page 16 2000.03.02.016 401396 V. Description of the invention (3) Gas ethane and so on. The reaction time is usually in the range of 5 minutes to 72 hours. The reaction temperature is usually in the range of -20 t to the boiling point of the solvent used in the reaction or 100, and preferably from -5 t to the boiling point of the solvent used in the reaction or up to 1000 π. The molar ratio of the alcohol compound represented by the formula (Π) to the carboxylic acid reactive derivative represented by the formula (ii) may be determined according to need, but it is preferably an equal molar ratio or a ratio close to the equal molar ratio. The amount of the condensing agent or the base may be in the range from the molar amount to an excess, preferably from the molar amount to 5 molar, relative to the alcohol represented by 1 mole (U). After completion of the reaction, the reaction solution may be subjected to general subsequent treatments, such as extraction with an organic solvent, concentration, etc., to obtain the compound, and if necessary, it may be purified by a general procedure such as chromatography and distillation. The alcohol compound represented by the formula (Π) and the carboxyfluorene represented by the formula (m) can be prepared by a method described in EP-31199-A and the like. The compound exhibits controlling effects on, for example, harmful insects including the following arthropods: Lepidoptera: Mothidae, such as Chii 1 0suppre ssa 1 is, Cnaphalocrocis _inal is, Plod ia li1 InUJ cte 11 a); Spodoptera, such as Spodop tera 1 i tur. Denier, Pseudo 1 et ia separata, cabbage night moth (Mame_st, ra brassicae); Pieridae Such as cabbage cabbage white butterfly (Pier is gX-u9i vora); Cryptoceraidae such as AdoxoDhves sPp 'Spodoptera; Laminidae; Toxocidae; Plusiinae;

401396 V. Description of the invention 3 ~ nw Di I 89.3.0 6 Supplement; modified carboxyfluorenyl ester; nitroimidazolidine derivative, N-fluorene derivative, for example, N-fluorenyl-N'-methyl-N ' -(6-Amino-3-pyridylmethyl) acetamidine, a gasified hydrocarbon compound, for example, endosu If an [6, 7, 8, 9, 9, 10, 10-hexakis-1 , 5,5a, 6,9,9a-Hexahydro-6,9-methylene-2,4,3 -benzodioxathiepine oxide], insects must die (τ-ΒΗ〇 [1 , 2,3,4,5,6-hexahexacyclohexane] and 1,2-bis (aerophenyl) -2,2,2-trigas ethanol; benzamidine phenylurea compounds, for example, Ceflon (Chlorfluazuron) [l- (3, 5_Digas-4- (3-Gas-5-trifluoromethyl, 0-bit-2-yloxy) phenyl) -3- (2, 6-difluoro Benzyl) urea], teflubenzuron [l- (3,5-digas-2,4-difluorophenyl) -3- (2, 6-difluorophenylfluorenyl) urea ] And flufenoxuron [l- (4- (2- (4-Gas_4_trigasmethylphenoxy) -2_fluorophenyl] -3- (2,6-difluorobenzyl ) Urea], thiourea derivatives, for example, difenone (仏 3 [6111: 1 ^ 111'〇11) 1 ^-(2,6-diisopropyl-4-phenoxyphenyl) 4'- First Butyl carbodiimide], phenylpyrazole compounds, metilon (1 ^ 1: 1; 乂 & (1132〇11) [5-methoxy-3- (2-methoxyphenyl) -1 ， 3,4-pyridine-2- (3H) -one], bromopyrolat [4,4'-dibromo T acid isopropyl ester], tetrad if on [4- Phenylphenyl 2,4,5-trifluorobenzyl], chinomethionate [S, S-6-fluorenylquinone * Rolin-2,3-diyldithiocarbonate], pyridaben) [2-Third-butyl-5- (4-Third-butylbenzylsulfanyl) -4-aeroponin-3 (2H) -one], fenpyroximate [(E) -4 -[(l, 3 -dimethyl-5 -phenoxybipyridin-4-yl) methyleneaminooxymethyl] tributyl benzoate], tebufenpyrad [N-4-第Tributylfluorenyl) -4 -gas-3 -ethyl_1-1 -methyl-5-Π-pyrazole carboxamide], polynactins complex [tetranaphthyl bacteria

C: \ Program Files ^ ateiit \ 310179.ptc Page 17 2000.03.02.017 401396 V. Description of Invention (4) Yellow Root Tiger (Agrot is sege turn), Little Root Tiger (Agrot isi ps i Ion); Helicoverpa genus; Heliotis Genus; Plutella xylostella (P 1 ute 1 la xv 1 ost e 11 a); Parnara guttata; Tinea pell ion el la; T ineola bissel liella and so on. Diptera: Culex mosquitoes such as Cu 1 ex pi pi ens pal lens, Cu es tr itaeniorhvnchus; Aedes mosquitoes such as Aedes aegypt i and Aedes albopictus ); Anopheles genus such as Anopheles sinensis; C hir onom i dae; Muscidae (Muse a domes ti ca); Muscina s tabu Ians yellow Ventral it rope (Fann ia canicularis); Calliphoridae; Sarcophagidae; Ant homy i idae such as the species fly (Del ia p latura), onion fly (Delia ant iqua); Tephritidae; Drosophilidae; pSyChodidae; Simuliidae; Ifetidae (Tabanidae); Phoridae; Stomoxyidae; Ceratopogonidae; etc. Net wing order: German cockroach (B lattel 1 a german ica); smoke-colored dish (Periplaneta j_y_l igi nos a): American region (Perop 1 an… ajper ic ana); brown large magpie (Periplaneta br unnea); oriental Secrets (Blatta orientalist et al. Hymenoptera:

Page 7

Preparation Example 1 Under ice cooling, 2.06 g of (1R) -trans-3- (2-methylpropyl) -2,2-dimethylcyclopropanecarboxylic acid gaseous substance was added to 178 g of 2 to 5 , 6-tetrafluoro-4-methyl T-yl alcohol, 0.87 g of pyridine and 20 ml of a mixture of tetrakis, and the mixture was stirred at room temperature for 8 hours. Β The reaction mixture was poured into about 100 ml of ice water. Extract two aliquots with 100 mL of ethyl acetate. The combined ethyl acetate was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was subjected to silica gel column chromatography to obtain 2.75 g of purified (110-trans-3- ( 2-methyl-1-propenyl) -2,2_dimethylcyclopropanic acid 2,3,5,6-tetrafluoro-4-fluorenylbenzidine (this compound, yield 87%). 1H -NMR (internal standard; TMS, in CDC13) < 5 value (ppm): 1. 13 (S, 3H), 1. 30 (S, 3H), 1. 40 (d, 1H), 1. 71 (brs, 6H), 2.08 (dd, lH), 2.28 (brs, 3H), 4.88 (m, lH), 5.20 (dd, 2H) The following describes the formulation example. In the following examples, "part" means " "Part by weight". Preparation Example 1: Emulsifiable concentrate dissolves 20 parts of this compound in 65 parts of xylene, and 5 parts of Sorpol 3005X (surfactant; registered trademark of Toho Chemical Co., Ltd.) are added thereto, and the mixture is stirred uniformly 20% emulsifiable concentrate was prepared. Formulation Example 2: Wettable powder made 40 parts of this compound, first mixed with 5 parts of Sorpol 3005X (as above), then added 32 parts of Carplex # 80 (synthetic hydration and oxidation) Silicon

C: \ Program Files \ patent \ 310179.ptc Page 19, 2000.03.02.019 401896 V. Description of the invention (5) Formicidae; Vespidae; Bethylidae; Tenteredinidae ) Such as yellow-winged bee (

Atha1i a rosae i apοnen s i s), etc. Flea orders: Ct enocepha 1 i des can i s; cat flea (

Ctenocephalides fe 1 i s); human flea (Pur ex i rri tans) and so on. Lice: thoughtful wind (Pedi cu 1 us humanus humanus); yin wind (Phthirus Pubis); head disorder (Pedi cuius humanus capitis); Pediculus corpor is, etc. Isoptera: Reticul i termes sper atus; Coptotermes formosanus in Taiwan. Planthoppers such as Laodelphax str i atel 1 us, rice brown fly ILCNj laparvata lugens), white-backed fly JUSogatella furcif era); leafhoppers such as Nephot et tix c_i_nct i ceps, Micro green leaf zen (Nephot c11 ix vi rescens); Fangidae; Callidae; Whiteflies; Polygonaceae; Reticulidae; Psyllidae; Coleoptera: Attagenus uni col or japonicus, IKAuthrenus verbasci); corn rootworms such as Diabrotica vi rgi fera, Diabrotica undecimpuncta t_a how ar di, Scarabaeidae such as Anomala cuprea), Soybean Gold Turtle (Anomala

V. Description of the invention (6) rufocuprea), Weevils such as corn elephants (S i touh i1u s zeama is), rice elephants (L i ssorhoptrus oryzoph i1u s), ball weevil (Mall weevil), mung bean elephant (Ca 1 1 osobruchus ch i nens is); Tenebrionidae, such as Tenebrio mol itor, Tri i bo 1 i um cas taneum; Leaf family, such as rice negative mudworm (On 1 ema oryzae), yellow stripe jumper (Phy 11 o treta str i ο 1 ata) and yellow shougua (Au 1 a copho ra femoral is); Anobiidae, Epi 1 achna spp. ) Such as the big twenty-eight star ladybird (Ep i 1 achna vigintiocto punctata); the powdery family (Lyciidae); the long family (Bostrychidae); Cerambycidae; Paede rus fuscipes and so on. Hymenoptera: Thr i ps palm i, Thrips thrips, Thrips thrips (

Thr i ps hawa i i ens i s), etc. Orthoptera: Gryllotalpidae, Acrididae, etc. Mite ticks: Dermanyssidae, such as Dermatophagoides f ar i nae, and European dermatodes (

Dermat ophagoi des Dteronvssinus); Acaridae (; Araridaf〇 such as Ty rophagus putrescent i ae), Aleuroglyphus ovatus; Glycyphagidae such as G 1 vcvphagus pr ivatus, sweet home (Glycvi ^ hagus domest i cus)-G lycyphagus destructor; Cheyetidae #J

401396 V. Description of Invention (7)

Che lacarops is ma laccensi s, Chev 1 etus fort is; Tarsonemidae; Chortoglyphus; Haplichthoninus s_impi_ex; etc .; Tetranychi dae, such as Tetranychus urti cae, Tetranychus urti cae, Tetranvchus kanzawai), Panonychus ci tr i, Panonychus mIM; Ixodi ae, such as the small cattle tick (

Boophi1us microp lus), Haemaphysa 1 is s 1 ongi con is. The insecticide of the present invention is used to control or repel bookworms, especially insects and mites. When the compound is used as an active ingredient of an insecticide, it is usually mixed with a solid carrier, a liquid carrier, a gas carrier, or a bait, or impregnated into a mosquito coil or a matrix of an electric heating fumigation mat. The compound is used as a formulation such as an oil solution, an emulsifiable concentrate, a wettable powder, a flowable formulation (such as an aqueous suspension or an aqueous emulsion), granules, a fine powder, a gaseous agent, a volatile formulation such as a mosquito coil 、 Mosquito coil pads for electric heaters and liquid spraying from electric heaters, heating fumigants such as flammable fumigants, chemical fumigants, non-heating fuming agents, non-heating volatilization coated on resin or paper :, Pottery mist formulation, ULV formulation (ultra-low dosage formulation) and poison bait. When needed, add surfactant or other adjuvants to the formulation. ° Ingredients These formulations contain 0.001 to 95% by weight of the compound as a solid carrier for active formulations, including, for example, # 土 细粉 [eg, Shangling clay, diatomaceous earth, synthetic hydrated silica bentonite ~ Fubasami clay and acid clay], Hei Zhang's attacking violent moon, ceramics, others

401396 V. Description of the invention (8) No 4 minerals (for example, sericite, quartz, sulfur, activated carbon, carbon yogurt, and hydrated oxidized particles). Tanker carriers include, for example, water, alcohols (eg, methanol, ethanol), and ketones (eg, acetone, methyl ethyl ketone). Aromatic hydrocarbons (e.g., benzene, toluene, xylene, ethylbenzene, and methylnaphthalene), aliphatic hydrocarbons (e.g., hexane, cyclohexane, kerosene, and gasoline), esters (e.g., ethyl acetate, Butyl acetate), nitriles (e.g., acetonitrile, isobutyronitrile), ethers (e.g., diisopropylammonium, disulfonate), amidines (e.g., N, N-dimethylformamide, N , N-dimethylacetamide), functional hydrocarbons (for example, digas methane, trigas ethane, tetragas carbon), dimethyl methylene maple, and vegetable oils (for example, soybean oil, cottonseed oil) . Gas carriers or propellants for formulation include, for example, Freon gas, butane gas, LPG (liquid petroleum gas), dimethyl ether, and carbon dioxide. Surfactants including, for example, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene alkyl aryl ethers, polyethylene glycol ethers, polyol esters And sugar alcohol derivatives. Binders, dispersants, and other adjuvants, including, for example, casein, gelatin, polysaccharides (eg, starch, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, sugar, and synthetic water-soluble Polymer (for example, enol polyvinylpyrrolidone, polyacrylic acid). Stabilizers include, for example: isopropyl phosphate (acrylic acid), beta- (2δ-bis-third-butyl_4-methyl), compounds, second butyl_4-methoxyphenol and 3-tert-butyl A mixture of 4--4-methoxyphenol. Oils, mineral oils, surfactants, fatty acids and fatty acid esters

* 401396 V. Description of the invention (9) Mixture of wood powder and pyrethrum powder) and deadening agent [such as Tabu powder (powder of MachUus thunbergj i), starch or gluten]. The base material for mosquito coils used for electric heating is a compacted fibril sheet such as cotton wool or a mixture of wool and pulp. The base materials used in flammable fumigants include, for example, exothermic end acid salts, nitrites, guanidine salts, potassium gas acid, ethyl cellulose and wood flour), pyrolysis Agents (such as alkali metal tritium salts, salts, dichromates and chromates), oxygen supply sources (such as nitric acid), combustion aids (such as melamine, wheat starch), fillers (such as Cementing agent (such as synthetic glutinous paste). The base material in the furnace Si-based brightener contains, for example: exothermic agents (such as alkali metal sulfides, polysulfides, hydrogen sulfides, hydrated salts, gasification metallizing agents (Such as carbonaceous materials, iron carbide and activated clay), yes, azomethoxamine, sulfenylhydrazine, N, N, _dinitrosopentaquinone (such as polystyrene, polyaminomethyl Acid esters), and fillers (such as Λ-tetramine, vitamins). Then 1 ^ cavitation ... 'fiber or synthetic fiber base materials for non-thermal volatile formulations include examples, filter paper and Japanese paper. Thermoplastic resin 1 $ Ϊ 动Hexamethylene chloride (aqueous suspension or aqueous emulsion) usually * Μ coffee compound is dispersed in a sentence containing "to 15% points :: 广 由

The base materials used on page 12 include, for example, ingredients, compounds, crystalline cellulose, antioxidants (such as dibutyl noodles = 1: dihydroguaiaretic acid), and substances that prevent accidental eating (such as Red pepper dimethicone, agent (pneumolactone flavoring agent, onion flavoring agent, peanut oil bu bow 1 lure 401396 V. Description of invention (ίο) to 10% suspension aid (such as protective colloid or thixotropic compound) And 0 to 10% of additives (such as defoaming agents, anti-corrosive agents, stabilizers, extenders, penetration aids, antifreeze agents, fungicides, fungicides) in water. This compound is generally insoluble in In this case, the compound can be dispersed in oil to obtain an oily suspension. Protective colloids include, for example, gelatin, casein, various gums, cellulose vinegars, and polyvinyl alcohol. Thixotropic compounds include, for example: Bentonite, magnesium aluminum silicate, xanthan gum and polyacrylic acid can be used directly or diluted with water. These formulations can be used with other insecticides, acaricides, repellents or synergists. Without mixing or pre-mixing The above insecticides and acaricides include, for example, organophosphates, for example, fenitrothion [0,0 -dimethyl0- (3-methyl-4 -nitrophenyl) thiolin Acid esters], fenthion [0,0-diylmethyl〇 ((3-methyl-4- (methylthio) phenyl) phosphorothioate], diazinon [0, 〇-diethyl 0-2 -isopropyl-6-methyl sulfol-4-yl thiocyanate], Taosson (<: 111〇171 ^?} 1〇3) [0,0- Diethyl-0-3,5,6-trisyl-2-pyridylthiophosphonic acid ester], acephate [0, S-dimethylacetamidothiocarbamidine], Methamone (11161: 111 (1 & 1: 1 ^ 〇11) [8-2,3-dihydro-5-methoxy-2 -oxo-1,3,4-thiadiazole-3 -yl Methyl 0,0-difluorenyl dithiophosphate], di su 1 foton [0, 0-diethyl S-2-ethylthioethyl dithio bowl acid vinegar], two DDVP [2,2-Ethyl ethyl dimethyl 4 acid vinegar], sulprofos [0-ethyl 0-4- (fluorenylthio) phenyl $ -propyldithio Phosphate ester], cyanophos [〇-4-helylphenyl 〇, 〇_dimethyl

Page 13 V. Description of the invention (11) Phosphorothioate], dioxabenzofos [2-methoxy-4H '• 1,3,2-benzodiphosphonium-2- Sulfide], Diphenanthrene ((1 丨 托 1 ^ 〇316) [〇, 〇-dimethyl S- (N-methylamine formamidine methyl) dithiophosphate], rice phenthoate [2-Dimethoxyphosphinothio (phenyl) ethyl acetate], marathion [diethyl (dimethoxyphosphinothiothio) succinate], trichlorfon [2,2,2-Trisamino-1-hydroxyethylphosphonic acid dimethyl], azonphos-methyl [S-3,4_ dihydro-4-oxo-1,2, 3 -Benzotrigenol-3 -ylmethyl 0,0-dimethyldithiophosphate], yazoline 〇011〇 <: 1′〇1: 〇? 11〇8) [(£) 1-methyl-2- (fluorenamidinyl) ethylene dimethyl phosphate], and ethion [0, 0,0,, 0, -tetraethyl S, S'-methylene Bis (dithiofillate)]; aminoammonium ester compounds, for example, butyl chlorphenirate (BPMC) [2-second butyl benzylamine sulfonate], benfracarb [ N- [2, 3 -Dihydro-2, 2 -dimethylbenzofuran-7-yloxoyl (methyl) amine [] -N-isopropyl-cold-alanine ethyl ester], propoxur [2-isopropyloxybenzyl N-methylaminophosphonate], carbosulfan [2, 3 -Dihydro-2, 2-dimethyl-7-benzo [b] furanyl N-dibutylaminethio-N-fluorenyl carbamate], carbary [[naphthyl N-fluorenyl] Carbamate], methomyl [s_methyl N _ [(methylamine methyl group) oxy] thioethyl imidate], ethiofencarb [2- ( Ethylthiomethyl) phenylmethylcarbamate], & 1 (11〇31 ^) [2-methyl ~ 2- (methylthio) propanal 0-methylamine 曱 醯Oxime], oxamyl [N, N ~ dimethyl-2_amidomethylamidooxyimino_2_ (fluorenylthio) acetamido], and fenothhicarb ) [s _ (_ 4_phenoxybutyl) N, N —methylthiocarbamate] 丨 pyrethroid

Page 14 Public Left SS87118115

Amendment V. Explanation of the invention (12) Compounds, for example, etfenenx [2- (4-ethoxyphenyl) -2-methylpropyl-3-phenylhydrobenzyl mystery], Fenber Fenvaierate [(RS) -a-fluoro-3-phenoxybenzyl (rs) -2- (4-phenyl) -3-fluorenylbutyrate], Yifenbury (63 { 61 ^ & 16 ^ 士 6) [(3)-«-| 1yl-3-phenoxybenzyl (5) -2- (4-aminobenzyl) -3-methylbutyric acid vinegar], fen Fenpr〇pathrin URS)-~ cyano-3-phenoxybenzyl 2, 2, 3, 3-tetramethylcyclopropanecarboxylate], cypermethrin [(RS) _a_ 氱_3_phenoxyfluorenyl (1RS) -cis, trans-3_ (2,2-digasvinyl) -2,2-dimethylcyclopropane sulfonate], permethrin ) [(lRS) -cis, trans-3- (2,2-difluorovinyl) -2,2-dimethylcyclopropanecarboxylic acid 3-phenoxy vinegar], cyhalothrin [(RS) -a-fluoro-3-phenoxy T-group (Z)-(IRS) -cis-3- (2-amino-3, 3, 3 -trifluoroprop-butenyl)- 2, 2-Amidinocyclopropane acetic acid vinegar], deltamethrin [(S) -a ~ fluoro-3 -phenoxy (ir) -cis- 3- (2, 2- Dibromovinyl) -2,2-dimethylcyclopropane vinegar], Cycloprine (CyCl〇pr〇thrin) [(RS) -a ~ Gasoyl-3 -phenoxyTyl (RS) -2, 2-dioxo-1- (4-ethoxyphenyl) cyclopropanecarboxylate ], Fluvalinate (a-fluoro-3-phenoxyT-group N- (2-amino-α, α, trifluoro-p-tolyl) -D-valinate), bifennine (1 ^ [6111 ^ 1 ^ 1〇 [2-methylbiphenyl-3-ylmethyl) (2)-(11 ^) _ cis-3- (2-amino-3, 3, 3-trifluoro Allyl-1-enyl) -2,2-dimethylcyclopropanecarboxylate, 2-methyl-2- (4-bromodifluoromethoxyphenyl) propyl (3-phenoxybenzyl) Mystery, tralomethrin [(S) -α-cyano-3-phenoxybenzyl (1R-cis) 3 {(1RS) (1,2,2,2-tetrabromoethyl)} -2,2-dimethylcyclopropanecarboxylate], silafluofen [(4-ethoxyphenyl) {3- (4-

C: \ Program Files ^) atent \ 310179.ptc Page 15 2000. 03.02.015 Amendment 401396 LUtf V. Description of the invention (13) Monofluoro-3 -phenoxyphenyl) propyl} Tosoheptane] , D-phenothrin [3-phenoxybenzyl (1R)-cis, trans)-chrysanthemum] fenfenine (〇7 卩 1 ^ 11〇1: 111'111) [(1 ^)-〇: -cyano-3-phenoxybenzyl (11? -Cis, trans) -permethrin], d-resmethrin [5-fluorenyl-3-咲 Methyl (1R-cis, trans) _chrysanthemic acid vinegar], acrinthrin [(S) -α-fluorenyl-3-phenoxybenzyl (1R-cis (z)) -(2, 2-Difluorenyl-3- {3-oxo-3- (1,1,1,3,3,3-hexafluoropropoxy) propenyl} cyclopropanecarboxylate], Sai Cyfluthrin [(RS) -a-fluorenyl-4-fluoroyl-3-phenoxybenzyl 3- (2, 2-difluorovinyl) -2, 2-dimethylcyclopropanecarboxylic acid Esters], Deflunin (± 60111: 111: 111) [2,3,5,6-Tetrafluoro-4-methylbenzyl (11 ^ -cis (Z))-3- (2 -Gasyl-3, 3,3 -trifluoroprop-benyl) -2,2-dimethylcyclopropane vinegar], transfluthrin [2,3,5,6-tetra Fluoro (1R-trans) -3- (2, 2 -digas vinyl -2,2-Dimethylcyclopropanecarboxylic acid vinegar], tetramethrin [3,4,5,6-Tetraargonphthalimide hydrazone (1RS) -cis, trans-chrysanthemic acid Esters], al lethrin [(RS) -3-allyl-2-methyl-4-oxocyclopent-2-enyl (1RS) -cis, trans-chrysanthemate ], Pallethrin (; (s) _2-methyl_4_oxo_3_ (2-propanyl) cyclopent-2-enyl (1R) _cis, trans-chrysanthemic acid Ester], empenthrin [(RS) -buethynyl-2 -methyl-2-pentenyl (1R) -cis'-trans-chrysanthematate], imipr〇thrin [2,5-Dioxo-3- (prop-2-ynyl) imidazolidinylmethyl (1R) _cis, trans_2, 2-dimethyl-3- (2-fluorenylpropane -1-alkenyl) cyclopropanecarboxylate], d_fUramethrin [5- (2-propynyl) furyl (1R) _cis, trans-chrysanthenic acid]], and 5- ( 2-propynyl) furanmethyl 2,2,3,3-tetramethylcyclopropane

C: \ Program Files \ patent \ 310179.ptc Page 16 2000.03.02.016 401396 V. Description of the invention 3 ~ nw II I 89.3.0 6 Supplement; Modified Carboxamidine Ester; Nitroimidazolium Derivatives, N-Samarium Derivatives Compounds, for example, N-fluorenyl-N'-methyl-N '-(6-amino-3-pyridylmethyl) acetamidine, gasified hydrocarbon compounds, for example, endosu If an [6 , 7,8,9,10,10-hexafluoro-1,5,5a, 6,9,9a-hexahydro-6, 9-methylene-2,4,3 -benzodifluorene Benzodioxathiepine oxide], worms must die (τ-ΒΗ〇 [1,2,3,4,5,6-hexahexacyclohexane] and 1,2-bis (aerophenyl) -2, 2, 2 -Trigas ethanol; benzamidine phenylurea compounds, for example, chlorfluazuron [l- (3, 5_digas-4- (3-gas-5-trifluoromethyl) Alkoxy) phenyl) -3- (2,6-difluorobenzyl) urea], teflubenzuron [l- (3,5-digas-2,4-difluorophenyl ) -3- (2, 6-difluorophenylfluorenyl) urea] and flufenoxuron [l- (4- (2- -4_trifluoromethylphenoxy) -2_fluoro Phenyl] -3- (2,6-difluorobenzyl) urea], thiourea derivatives, for example, difenone (隆 3 [6111: 1 ^ 111'〇11) 1 ^-(2,6-diisopropyl-4-phenoxyphenyl) 4'-third butyl carbodiimide], phenylpyrazole compounds, metdilon ( 1 ^ 1: 〇 乂 & (1132〇11) [5-methoxy-3- (2-methoxyphenyl) -1,3,4-fluorenediureth-2- (3H) -one], Bromopyrolat [Isopropyl 4,4'-dibromo T acid], tetrad if on [4-Acetophenyl 2, 4, 5-trifluorobenzene maple], Titanium (Chinomethionate) [S, S-6-fluorenylquinone * Ruolin-2,3-diyldithiocarbonate], pyridaben [2-thirdbutyl-5- (4-thirdbutyl Benzylthio) -4-paphen-3 (2H) -one], fenpyroximate [(E) -4-[(l, 3-dimethyl-5 -phenoxy) -4-yl) dimethylaminooxymethyl] tert-butyl benzate], tebufenpyrad [N-4-tertiary butyl fluorenyl)-4-gas-3-ethyl _ 1 _ Methyl-5-Π-pyrazole carboxamide], polynactins complex [tetranaphthyl

C: \ Program Files ^ ateiit \ 310179.ptc Page 17 2000.03.02.017 401396 V. Description of the invention (15) phytoxins, dicetin and trinaphsin], pyrimidifen [5- 气 -N -[2- {4- (2 -Ethoxyhexyl) -2,3 -difluorenylphenoxy 丨 ethyl] _6_hexyl-4-amine], milbemectin, imifen Examples of abamitectin, ivermectin, and azadirachtin [AZAD] β repellents such as 3, 4-fluorenediol, ν, N-diethyl-m-toluidine, 2- (2-Hydroxyethyl) -1-hexahydropyridinecarboxylic acid, bupropyl propyl ester, p-gay-3,8-secondase, vegetable essential oils (such as hyssop oil). Examples of synergists are bis- (2,3,3,3-tetrakistriol) (3-421), N_ (2-ethylhexyl) bicyclo [2. 2. 1] hept-5-dilute-2 , 3 -dicarbonimine (MGK-2 64) and α- [2- (2-butoxyethoxy) ethoxy] _4,5-methylenedioxy-2-propyltoluene (piperazine oxidation Thing). When the compound is used as an active ingredient of a pesticide for household or animal health, the emulsifiable concentrate, the wettable powder, and the flowable formulation are diluted with water to a concentration of from 0.1 to 1,000 ppm. use. Oil solutions, smoke sprays, fumigants, volatile agents, mist generators, ULV tinctures, poison baits, and resin formulations are used directly. »The amount and concentration of application can be based on the type of formulation, application time, and application. The place, application method, type of harmful insects and degree of damage vary. The compound exhibits better pest control effects with or without evaporation under heating. Therefore, it is particularly used as an active ingredient for household insecticides. The present invention will be described in further detail with reference to the following preparation examples, preparation examples and biological test examples; however, the present invention is not limited to these examples.

Page 18

Preparation Example 1 Under ice cooling, 2.06 g of (1R) -trans-3- (2-methylpropyl) -2,2-dimethylcyclopropanecarboxylic acid gaseous substance was added to 178 g of 2 to 5 , 6-tetrafluoro-4-methyl T-yl alcohol, 0.87 g of pyridine and 20 ml of a mixture of tetrakis, and the mixture was stirred at room temperature for 8 hours. Β The reaction mixture was poured into about 100 ml of ice water. Extract two aliquots with 100 mL of ethyl acetate. The combined ethyl acetate was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain a crude product, which was subjected to silica gel column chromatography to obtain 2.75 g of purified (110-trans-3- ( 2-methyl-1-propenyl) -2,2_dimethylcyclopropanic acid 2,3,5,6-tetrafluoro-4-fluorenylbenzidine (this compound, yield 87%). 1H -NMR (internal standard; TMS, in CDC13) < 5 value (ppm): 1. 13 (S, 3H), 1. 30 (S, 3H), 1. 40 (d, 1H), 1. 71 (brs, 6H), 2.08 (dd, lH), 2.28 (brs, 3H), 4.88 (m, lH), 5.20 (dd, 2H) The following describes the formulation example. In the following examples, "part" means " "Part by weight". Preparation Example 1: Emulsifiable concentrate dissolves 20 parts of this compound in 65 parts of xylene, and 5 parts of Sorpol 3005X (surfactant; registered trademark of Toho Chemical Co., Ltd.) are added thereto, and the mixture is stirred uniformly 20% emulsifiable concentrate was prepared. Formulation Example 2: Wettable powder made 40 parts of this compound, first mixed with 5 parts of Sorpol 3005X (as above), then added 32 parts of Carplex # 80 (synthetic hydration and oxidation) Silicon

C: \ Program Files \ patent \ 310179.ptc Page 19 2000.03.02.019 V. Fine powder of the description of the invention (17); registered trademark of Shiino Yoshi Co., Ltd.) and 23 copies of Shixuezao with 300 mesh. The mixer stirs the mixture uniformly to obtain 40% wettable powder. Formulation Example 3: Granules 1.5 parts of this compound and 98.5 parts of 40301 ^ 1 ^ 1 ^ 1 ^ 24/48 [OIL DR [Company calcined Montmor llonite product; granular carrier with a particle size of 24 to 48 meshes] uniformly mixed 'to obtain 5% particles of each compound. Formulation Example 4: Microcapsules 10 parts of the present compound, 10 parts of phenyl difluorenyl ethane and 05 parts of Sumidur L-75 (Dendrophenyl diisofluoro ester, available from Sumitomo Bayer Ester Co., Ltd. The company) mixture was added to 20 parts of a 10% acacia gum aqueous solution, followed by kneading with a homogenizer to prepare an emulsion having an average particle size. This emulsion was mixed with 2 parts of ethylene glycol and reacted in a 60 t warm water bath for 24 hours to prepare a microcapsule slurry. 0.2 parts of xanthan gum and 1.0 part of Beagum R (Chang acid Mingzhen, purchased from Sanyo Chemical Industry Co., Ltd.) were dispersed in 56.3 parts of ion-exchanged water to prepare a tung agent. Next, 42.5 parts of the above microcapsule slurry was mixed with 57.5 parts of a thickener to obtain a 10% microcapsule formulation. Formulation Example 5: Flowable Formulation Add a mixture of 10 parts of the compound and 10 parts of phenylxylylethane to 20 parts of a 10% aqueous solution of polyethylene glycol, and then stir with a homogenizer to obtain an average particle. 3 / zin emulsion. 401396 V. Description of the invention (18) Disperse 0.2 part of xanthan gum and 1.0 part of Beagum R (aspartic acid 1§, from Sanyo Chemical Industry Co., Ltd.) in 588 parts of ion-exchanged water to prepare a thickener. Then, 40 parts of the above-mentioned emulsion was mixed with 60 parts of a thickener to obtain a 5% flowable formulation. Preparation Example 6: Powder Mix 5 parts of this compound with 3 parts of Carplex # 80 (as described above), 0.3 parts of PAP and 9 1. 7 parts of 300 talc talc, mix with a mixer to obtain 5% powder. Preparation Example 7: Oil solution First, 0.1 part of the compound was dissolved in 5 parts of digas methane, and then mixed with 94.9 parts of deodorized kerosene to obtain a 0.1% oil solution. Preparation Example 8: Oily aerosol spray A solution prepared by dissolving 1 part of the compound in 5 parts of dichloromethane and 34 parts of deodorized kerosene was put into an air atomizing container. Thereafter, a valve was set in the container, and 60 parts of a propellant (liquefied petroleum gas) was fed under the pressure through the valve to obtain an oily aerosol spray. Preparation Example 9: Water-based aerosol spray A mixture of 50 parts of pure water and 0.6 part of the compound, 5 parts of xylene, 3.4 parts of deodorized kerosene, and 1 part of ATMOS (emulsifier; registered trademark of Atlas Chemical Co., Ltd.) Aerosolized container order. Then, a valve is set on the container, and 40 parts of propellant (liquefied petroleum gas) is fed under pressure through the valve to obtain an aqueous aerosol spray. Preparation example 10: mosquito coil

401396

V. Explanation of the invention (19) A mixture of a solution prepared by dissolving 0.3 g of the compound in 20 ml of propidium and a carrier for 99 u mosquito coil (Tabu powder, pyrethrum residue and wood powder ratio 4: 3: 3 )mixing. This mixture was kneaded with 120 ml of water, molded, and dried to obtain a mosquito coil. Preparation Example 11: Electrothermal fumigant mosquito repellent 0.8 g of this compound and 0.04 g of piperonyl butoxi de were dissolved in acetone to prepare 10 ml of a solution. Then, 0.5 ml of this solution was uniformly impregnated into a base material (compact fibril sheet made of a mixture of pulp and cotton wool: 2.5 cm X 1.5 cm X 0.3 cm) to prepare a mosquito repellent pad. Preparation Example 12: Electrothermal fumigation type solution 3 parts of this compound were dissolved in 97 parts of deodorized kerosene. Pour this solution into a polyethylene gas container. A porous absorbent lamp core obtained by solidifying an inorganic powder with a binder and sintering is inserted into a container (the upper end portion of the lamp core can be heated by a heater) 'to produce an electric fume device using a liquid. Preparation Example 13: Fumigant A porous ceramic plate (4.0 cm x 4.0 cm x 1.2 cm) was impregnated with a solution prepared by dissolving 100 mg of the compound in an appropriate amount of acetone to prepare a fumigant. Preparation Example 14: Volatile agent A solution prepared by dissolving 100 micrograms of the present compound in an appropriate amount of propion was coated on filter paper (2.0 cm x 2.0 cm x 0.3 min), and then acetone was evaporated to obtain a volatile agent. Formulation Example 15: Acaricidal tablets The filter paper was impregnated with an acetone solution containing the compound to make the compound concentrated

Page 22 V. Description of the invention (20) The degree of lg / liri is 1 gram per square meter ', and then propidium is evaporated to prepare an acaricid tablet. The present compound was tested as an active ingredient of a pesticide. Biological Test Example 1; Insecticide test on housefly. A filter paper with a diameter of 5.5 cm was laid on the bottom of a polyethylene cup (diameter: 5.5 cm). After the 500 ppm aqueous emulsion obtained by emulsifying the concentrate was dropped on the filter paper, about 30 mg of sucrose as a bait was uniformly sprinkled. Ten female houseflies with low sensitivity to pyrethroids were placed in the cups, and the mortality rate was examined after being capped for days. As a result, the present compound was found to exhibit a mortality rate of 100%. In contrast, in the treatment group without emulsifying concentrate without active ingredient, the mortality rate was 0%. Biological test example 2; Insecticide test for German 蠊 蠊 将 Filter paper with a diameter of 5.5 cm was laid on the bottom of a polyethylene cup (diameter: 55 cm). After 0.7 ml of a 500 ppm aqueous emulsion obtained by diluting the emulsifiable concentrate of the present compound prepared as in Preparation Example 1 was dropped on a filter paper, about 30 mg of sucrose as a bait was spread evenly. Two female German 4s with low sensitivity to pyrethroids were placed in the cup and covered. After 6 days, mortality was reviewed. As a result, the present compound was found to exhibit a mortality rate of 100%. Conversely, in the treatment group without emulsifying concentrate containing active ingredients, the mortality rate was 0%. Biological Test Example 3; Insecticide test on common mosquitoes. The aqueous emulsion obtained from the emulsifiable concentrate was added to 100 ml of ion-exchanged water (active ingredient concentration: 3.5 ppm). Twenty last-instar larvae of common mosquitoes (Red house mosquito) were placed in the water. After one day, the mortality of common mosquitoes was examined. Judged by

Page 23 401396 V. Description of the invention (21) Estimated results. a: 90% or higher mortality rate b: 10% or higher, but lower than 90% mortality rate c: 10% or lower mortality rate The results show that the compound has been evaluated as a, with no active ingredients The emulsifiable concentrate handler was evaluated as c. Biological test 4, · Insecticide test on housefly The acetone dilution of the compound was applied to the rear chest area of 10 female house ropes (active ingredient: 5 " g / l housefly), and water and Food to housefly. After 24 hours, review the dying percentage twice.) It was found that the present compound exhibited a 100% dying percentage. In contrast, the dying percentage in the acetone-treated group without the active ingredient was 0%. Biological test example 5; Insecticide test on housefly (volatility at room temperature) 0.64 ml of a 0.05 (W / V)% acetone solution of the compound was dropped onto an aluminum pan (bottom diameter: 7 cm ), Followed by air-drying the acetone. A female housefly was placed in a polyethylene cup (diameter: 9 cm; depth: 4.5 cm) 'and the cup was sealed with a 16-mesh nylon mesh to prevent the housefly from coming into direct contact with the compound. Place the cup with the mouth of the cup facing down on the pan, and leave it at 25 ° C for 120 minutes. Then remove the cup from the aluminum pan 'and provide water and food to the home rope. Examination of the dying percentage (repeat twice) after 24 hours 8 found that the compound exhibited a dying percentage of 1QQ%. Relatively, the acetone-treated group containing no active ingredients had a dying percentage of Biological Test Example 6; insecticidal test on E. reticulata. The compound diluted with acetone to a predetermined concentration was applied to 10 reticulate clothing.

Page 401396

The central part of the back of the middle age larvae of the moth makes the dose of active ingredient 3 micrograms per worm. Wool calico (2 cm x 2 cm size) is used as & food for net moths. After 7 days ’look at the percentage of dying and the damage to the wool print (repeat twice). The degree of damage was evaluated as follows: + + +: Extreme damage + +: Serious damage +: Slight damage, 1: Undamaged It was found that the compound exhibited 100% mortality and the degree of damage was —. In contrast, the death disc helmet in the propionate treatment group containing no active ingredients was {〇%, and the degree of damage was + + +. '' Biological test example 7; insecticidal test on reticulate moth (function at room temperature) Wool printed cloth (2 cm, X 2 cm size) was placed on the bottom of a polyethylene cup (bottom diameter: 10 cm, opening Partial diameter: 12.5 cm, height: 95 cm '(volume: 950,000 cm3). Ten middle-instar larvae of the reticulata moth were placed in a cup, and the lid was suspended, and the volatile agent prepared as in Preparation Example 14 was hung in the cup from the lid. After standing at 25 t for 1 week, the cup was opened, and the percentage of dying u ratio and the degree of damage to the moth by moth (repeated twice) were assessed. The damage was evaluated as follows: + + +: extreme damage + +: Severely Impaired +: Slightly Impaired—: Uninjured fruit found 'this compound exhibits a dying percentage of 100%; course of impairment

Page 25 5. Description of the invention (23) The degree is one. In contrast, in the acetone-treated group without active ingredients, the percentage of dying was 0%, and the degree of damage was ++ +. In this test, no change in filter paper color or unpleasant odor was observed just after the treatment or after one week of treatment. Biological test 8; Insecticide test on common mosquitoes (volatilization effect at room temperature) 0.64 ml of a 0.05 (ff / V)% propidium solution of the compound (1) was dropped onto a name plate (bottom diameter: 7 cm), then Bing Ming was air-dried. 10 piles of common mosquitoes (House mosquito) were placed in a polyethylene cup (diameter: 9 cm, depth: 4.5 cm), and the cup was sealed with a 16 mesh nylon mesh to prevent direct contact between the mosquito and the compound . Place the cup with the mouth of the cup facing down on the aluminum pan and leave it at 2 5 ° c for 120 minutes. Then remove the cup from the aluminum pan and provide water and food to the mosquitoes. After 24 hours, check the percentage of dying (repeated twice) ^ (11〇_trans-chrysanthemic 4-dilutel 3, 5, 6-tetrafluoromethylene ester (hereinafter referred to as " compound a ") and ( 1R) -trans-chrysanthemic acid 2, 3, 5'6-tetrafluoro-4-methoxyfluorenyl ester (hereinafter referred to as "Compound B") was subjected to the same test, and the results are shown in Table 1. 401396 [表1] V. Description of the invention (24) D'T test area 丨 Dose (mg / m2) 1-+ Percent dying (%) This compound treated area 1 0.625 1 70 1 1.25 1 85-+ Compound A treated area 1 0.625 1 0 1 1.25 I 15-+. Compound B treatment zone 1 0.625 1 0 1 + —— 1.25 1-+-40 Propionate treatment zone without active ingredients 1 1 丄 1 1. 丄 0 Page 27

Claims (1)

401396 Case No. 87118115 39., 3. 06 :: λ · μ) :: -Ψ r'i U Modified Luo :: 丨 六 、 Applicable patent scope 1 .. τ The following formula (1R) -trans_ 3- (2 ~ • methyl-1-propenyl) -2,2-methylcyclopropanecarboxylic acid 2,3,5,6-tetrafluoro-4-methyl T ester: 2. —Species insecticidal composition, including (1R) -trans-3- (2-methyl-propenyl) -2, 2-dimethylcyclopropanecarboxylic acid 2, 3, 5, 6- Tetrafluoro-4-methylphosphonium ester is used as the active ingredient and carrier. 3. If the insecticidal composition of item 2 of the patent application is used for household insecticidal purposes. 4. A method for controlling pests, comprising (1R) -trans-3- (2-methyl-propenyl) -2,2-dimethylcyclopropanecarboxylic acid 2, 3, 5, 6-tetra Fluoro-4-methyl T ester is applied to the pest or the habitat of the pest. C: \ Program Files \ patent \ 310179.ptc Page 1 2000. 03. 02. 028 401396 Case No. 87118115 39., 3. 06 :: λ · μ) :: -Ψ r'i U Modified Luo :: 丨六 、 Applicable patent scope 1 .. τ kinds of the following formula (1R) -trans_3- (2 ~ • methyl-1-propenyl) -2,2_methylcyclopropanecarboxylic acid 2,3, 5, 6-tetrafluoro-4-methyl T ester: 2. —Species insecticidal composition, including (1R) -trans-3- (2-methyl-propenyl) -2, 2-dimethylcyclopropanecarboxylic acid 2, 3, 5, 6- Tetrafluoro-4-methylphosphonium ester is used as the active ingredient and carrier. 3. If the insecticidal composition of item 2 of the patent application is used for household insecticidal purposes. 4. A method for controlling pests, comprising (1R) -trans-3- (2-methyl-propenyl) -2,2-dimethylcyclopropanecarboxylic acid 2, 3, 5, 6-tetra Fluoro-4-methyl T ester is applied to the pest or the habitat of the pest. C: \ Program Files \ patent \ 310179.ptc Page 1 2000. 03. 02. 028